The aim of this article is to develop a better understanding of the educational pathways experienced by Haitian youth in Montreal when it comes to their post-secondary studies. The qualitative analysis of their life stories within the educational and learning pathways framework (Doray, 2011) reveals an assortment of pathways. Many are characterized by various sources of constraint (financial, institutional, social) and negative experiences with guidance counsellors during the transition to post-secondary studies. Perceived discrimination and racism also emerge as significant themes in the students’ discourses. In conclusion, future research and intervention strategies are suggested.